Identification

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Name
Cefdinir
Accession Number
DB00535  (APRD00644)
Type
Small Molecule
Groups
Approved
Description

Cefdinir, also known as Omnicef, is a semi-synthetic, broad-spectrum antibiotic belonging to the third generation of the cephalosporin class. It has been proven to be effective for the treatment of common bacterial infections in the ear, sinus, throat, lungs, and skin. Cefdinir was approved by the FDA in 1997 to treat a variety of mild to moderate infections and was initially marketed by Abbvie.6,16 Because of its chemical structure, it is effective against organisms that are resistant to first-line cephalosporin therapy due to the production of beta-lactamase enzymes.2,3

Structure
Thumb
Synonyms
  • (6R,7R,Z)-7-(2-(2-aminothiazol-4-yl)-2-(hydroxyimino)acetamido)-8-oxo-3-vinyl-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid
  • (6R,7R)-7-{2-(2-Amino-thiazol-4-yl)-2-[(Z)-hydroxyimino]-acetylamino}-8-oxo-3-vinyl-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid
  • Cefdinir
  • Cefdinirum
  • CFDN
External IDs
BMY-28488 / CI 983 / CI-983 / FK 482 / FK-482
Product Ingredients
IngredientUNIICASInChI Key
Cefdinir monohydrate6E7SN358SE213978-34-8QWUVJQSNISEEQI-KYIYMPJCSA-N
Product Images
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
OmnicefPowder, for suspension125 mg/5mLOralAbbvie1997-12-042011-05-31Us
OmnicefCapsule300 mg/1OralAbbvie1997-12-042011-05-31Us
OmnicefPowder, for suspension250 mg/5mLOralPhysicians Total Care, Inc.1997-12-042012-06-30Us
OmnicefPowder, for suspension250 mg/5mLOralAbbvie1997-12-042011-05-31Us
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
CefdinirPowder, for suspension250 mg/5mLOralA-S Medication Solutions2007-05-08Not applicableUs
CefdinirCapsule300 mg/1OralAvera McKennan Hospital2016-05-192018-07-09Us
CefdinirCapsule300 mg/1OralOrchidPharma Inc2014-07-042019-12-31Us
CefdinirPowder, for suspension250 mg/5mLOralPreferred Pharmaceuticals Inc.2018-09-14Not applicableUs
CefdinirCapsule300 mg/1OralRebel Distributors2011-01-14Not applicableUs
CefdinirCapsule300 mg/1OralRebel Distributors2008-01-07Not applicableUs
CefdinirPowder, for suspension250 mg/5mLOralSandoz2007-04-06Not applicableUs
CefdinirPowder, for suspension250 mg/5mLOralPar Pharmaceutical2014-05-012017-09-30Us
CefdinirCapsule300 mg/1OralPD-Rx Pharmaceuticals, Inc.2007-04-06Not applicableUs
CefdinirPowder, for suspension250 mg/5mLOralREMEDYREPACK INC.2019-05-13Not applicableUs
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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International/Other Brands
Cednir (Abbott) / Cefdiel (Ranbaxy) / Cefzon (Astellas) / Duocef (Ranbaxy) / Efdinir (Incepta) / Idinir (Invision) / Kefnir (Glenmark) / Nirocef (Sel-J) / Oceph (Zuventus) / Omicef (Sel-J) / Omnicef R (Janssen) / Palacef (Renata) / Palcef (Renata) / Rtist (Lupin) / Samnir (Siam Bheasach) / Xi Fu Ni (Central Pharm) / Zefdinir (Zydus) / Zinir (FDC)
Categories
UNII
CI0FAO63WC
CAS number
91832-40-5
Weight
Average: 395.414
Monoisotopic: 395.035809931
Chemical Formula
C14H13N5O5S2
InChI Key
RTXOFQZKPXMALH-GHXIOONMSA-N
InChI
InChI=1S/C14H13N5O5S2/c1-2-5-3-25-12-8(11(21)19(12)9(5)13(22)23)17-10(20)7(18-24)6-4-26-14(15)16-6/h2,4,8,12,24H,1,3H2,(H2,15,16)(H,17,20)(H,22,23)/b18-7-/t8-,12-/m1/s1
IUPAC Name
(6R,7R)-7-[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-(N-hydroxyimino)acetamido]-3-ethenyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
SMILES
[H][C@]12SCC(C=C)=C(N1C(=O)[C@H]2NC(=O)C(=N/O)\C1=CSC(N)=N1)C(O)=O

Pharmacology

Indication

Cefdinir is indicated to treat acute bacterial otitis media, acute maxillary sinusitis, community-acquired (CA) pneumonia, acute bacterial exacerbations of chronic bronchitis, pharyngitis/tonsillitis, and uncomplicated skin and skin structure infections in children and adults.14,6

The organisms susceptible to cefdinir have been listed below in addition to their associated clinical condition that may be treated with cefdinir.14 Various beta-lactamase producing organisms may be treated, as indicated in certain sections below.

Respiratory Acute bacterial exacerbations of chronic bronchitis caused by Haemophilus influenzae, Haemophilus parainfluenzae, Streptococcus pneumoniae (penicillin-susceptible only), and Moraxella catarrhalis

Community-acquired pneumonia caused by Haemophilus influenzae, Haemophilus parainfluenzae, Streptococcus pneumoniae (penicillin-susceptible only), and Moraxella catarrhalis

Ear, nose, and throat Acute bacterial otitis media caused by Haemophilus influenzae, Moraxella catarrhalis, and Streptococcus pneumoniae (penicillin-susceptible only)

Tonsillitis caused by Streptococcus pyogenes

Pharyngitis caused by Streptococcus pyogenes

Acute maxillary sinusitis caused by Haemophilus pneumoniae and Streptococcus pneumoniae (penicillin-susceptible only), and Moraxella catarrhalis

Skin and skin structure infections

Uncomplicated skin and skin structure infections caused by Staphylococcus aureus and Streptococcus pyogenes

Associated Conditions
Pharmacodynamics

Cefdinir is a bacteriostatic agent that treats bacterial infections by interfering with cell wall synthesis.14 Cefdinir exerts broad-spectrum activity against a variety of gram-positive and gram-negative bacterial infections. It is effective against several beta-lactamase enzyme producing bacteria. As a result, many organisms that are resistant to other cephalosporins may be susceptible to cefdinir.3,4,19

Mechanism of action

Five-member thiazolidine rings that make up penicillins are replaced in cephalosporins by a six-member dihydrothiazine ring, conferring greater bactericidal activity. This This 6-member ring enables cefdinir and other cephalosporins to resist inactivation by certain bacterial enzymes.12

With a mechanism similar to other beta-lactam antibiotics, the bactericidal activity of cefdinir is caused by the inhibition of cell wall synthesis via binding to penicillin-binding proteins (PBPs). Cefdinir, like other cephalosporins, penetrates the bacterial cell wall, combats inactivation by beta-lactamase enzymes, and inactivates penicillin-binding proteins.12 This interferes with the final step of transpeptidation in cell walls, eventually leading to cell lysis, which eventually leads to the death of bacteria that are susceptible to this drug.2 Cefdinir has shown affinity to penicillin protein binding proteins 2 and 3. 7,8,9 It has also been shown to inhibit transpeptidase enzymes of various bacteria, which may play a role in its bactericidal action.10,11 One in vitro study suggests that cefdinir inhibits myeloperoxidase release extracellularly.13 The impact of this potential drug target in relation to its mechanism of action is unknown.

TargetActionsOrganism
APenicillin-binding protein 2
inhibitor
Neisseria gonorrhoeae
APBP3
inhibitor
Haemophilus influenzae
NMyeloperoxidase
inhibitor
Humans
UPeptidoglycan transpeptidase
inhibitor
Additional Data Available
Adverse Effects

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Contraindications

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Absorption

Maximal plasma cefdinir concentration can be attained between 2-4 hours after an ingested dose.14 The bioavailability of cefdinir depends on the formulation used. The estimated bioavailability of cefdinir in the capsule form is approximately 16%-21%, depending on the dose. Absolute bioavailability after the administration of a suspension of cefdinir is 25%.2. The Cmax of cefdinir is 1.60 μg/mL after a 300 mg dose with an AUC of 7.05. Cmax is 2.87 μg/mL after a 600 mg dose with an AUC of 11.14 A meal high in fat can reduce the absorption of cefdinir by up to 15%, however, this is not a cause for clinically significant changes, therefore cefdinir may be taken with or without food.14 When given with aluminum or magnesium-containing antacids or iron, cefdinir absorption may decrease. It is recommended to allow 2 hours between cefdinir administration and the administration of these agents.2

Volume of distribution

The average volume of distribution of cefdinir in adults is about 0.35 L/kg and 0.67 L/kg in children.14,20 Another resource estimates the volume of distribution in adults at 1.56–2.09 L/kg.2 Cefdinir is found to be distributed in various tissues at clinically effective concentrations. It may be found in the epithelial lining fluid, bronchial mucosa, tonsils, sinuses, skin blister fluid, as well as the middle ear fluid.2 Third-generation cephalosporins such as cefdinir cross the blood-brain barrier and are found in high concentrations in the cerebrospinal fluid, unlike their first and second generation counterparts.12 The wide tissue distribution of cefdinir allows it to treat a variety of infections throughout the body.

Protein binding

The plasma protein binding of cefdinir ranges from 60% to approximately 70%.2,14

Metabolism

This drug is not significantly metabolized and its pharmacological actions are mainly attributed to the parent drug.2,14

Route of elimination

This drug is mainly excreted by the kidneys. Dose adjustments may be required for patients with renal impairment or patients on dialysis.14 Approximately 18.4% of a 300 mg dose of cefdinir was found unchanged in the urine after a 300 mg dose was administered during a pharmacokinetic study of 21 individuals.20 A large proportion of the administered dose is excreted in the feces, although the majority is found in the urine.12

Half life

The average plasma elimination half-life is about 1.7 hours in adults.14 In children and healthy infants, plasma elimination half-life ranges from 1.2–1.5 hours.2

Clearance

The renal clearance in healthy adults in a pharmacokinetic study was 2.0 (± 1.0) mL/min/kg and the clearance in patients with renal failure was lower, decreasing in proportion to the degree of renal impairment.20 Dose adjustment is required in patients with renal impairment.14

Toxicity

LD50 information Oral LD50 of cefdinir in the rat is >2000 mg/kg.17

There are limited data regarding cefdinir overdose in the literature. In studies of rodents, one 5600-mg/kg dose administered orally did not lead to adverse effects. Signs of toxicity and overdose caused by other beta-lactam antibiotics included nausea, vomiting, diarrhea, abdominal pain, and seizures.18

Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
(R)-warfarinThe risk or severity of bleeding can be increased when Cefdinir is combined with (R)-warfarin.
(S)-WarfarinThe risk or severity of bleeding can be increased when Cefdinir is combined with (S)-Warfarin.
4-hydroxycoumarinThe risk or severity of bleeding can be increased when Cefdinir is combined with 4-hydroxycoumarin.
AbacavirCefdinir may decrease the excretion rate of Abacavir which could result in a higher serum level.
AbciximabThe therapeutic efficacy of Abciximab can be decreased when used in combination with Cefdinir.
AcarboseAcarbose may decrease the excretion rate of Cefdinir which could result in a higher serum level.
AceclofenacAceclofenac may decrease the excretion rate of Cefdinir which could result in a higher serum level.
AcemetacinAcemetacin may decrease the excretion rate of Cefdinir which could result in a higher serum level.
AcenocoumarolThe risk or severity of bleeding can be increased when Cefdinir is combined with Acenocoumarol.
AcetaminophenAcetaminophen may decrease the excretion rate of Cefdinir which could result in a higher serum level.
Additional Data Available
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    Extended Description

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  • Severity
    Severity

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  • Evidence Level
    Evidence Level

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Food Interactions
  • Avoid taking antacids at same time (up to 2 hours before or after antibiotic).
  • Avoid taking iron preparations at same time (up to 2 hours before or after antibiotic).
  • Take without regard to meals.

References

Synthesis Reference

Gwan Sun Lee, Young Kil Chang, Jong Pil Chun, Joon Hyung Koh, "Process for preparation of cefdinir." U.S. Patent US6093814, issued December, 1995.

US6093814
General References
  1. Kimura Y, Kawamura M, Owada M, Fujiwara T, Maesawa C, Hiramori K: Successful steroid therapy for cefdinir-induced acute tubulointerstitial nephritis with progressive renal failure. Intern Med. 2001 Feb;40(2):114-7. doi: 10.2169/internalmedicine.40.114. [PubMed:11300142]
  2. Perry CM, Scott LJ: Cefdinir: a review of its use in the management of mild-to-moderate bacterial infections. Drugs. 2004;64(13):1433-64. doi: 10.2165/00003495-200464130-00004. [PubMed:15212560]
  3. Guay DR: Pharmacodynamics and pharmacokinetics of cefdinir, an oral extended spectrum cephalosporin. Pediatr Infect Dis J. 2000 Dec;19(12 Suppl):S141-6. [PubMed:11144395]
  4. Paris MM, Devcich KJ: Overview of cefdinir: pharmacokinetics, safety, and efficacy in the treatment of uncomplicated skin and skin structure infections. Cutis. 2004 May;73(5 Suppl):14-8. [PubMed:15182160]
  5. Chen J, Ahmad J: Cefdinir-induced hepatotoxicity: potential hazards of inappropriate antibiotic use. J Gen Intern Med. 2008 Nov;23(11):1914-6. doi: 10.1007/s11606-008-0758-y. Epub 2008 Aug 28. [PubMed:18752027]
  6. Sader HS, Biedenbach DJ, Streit JM, Jones RN: Cefdinir activity against contemporary North American isolates from community-acquired urinary tract infections. Int J Antimicrob Agents. 2005 Jan;25(1):89-92. doi: 10.1016/j.ijantimicag.2004.07.006. [PubMed:15620832]
  7. Ochiai S, Sekiguchi S, Hayashi A, Shimadzu M, Ishiko H, Matsushima-Nishiwaki R, Kozawa O, Yasuda M, Deguchi T: Decreased affinity of mosaic-structure recombinant penicillin-binding protein 2 for oral cephalosporins in Neisseria gonorrhoeae. J Antimicrob Chemother. 2007 Jul;60(1):54-60. Epub 2007 May 31. [PubMed:17540669]
  8. Ferrer-Gonzalez E, Kaul M, Parhi AK, LaVoie EJ, Pilch DS: beta-Lactam Antibiotics with a High Affinity for PBP2 Act Synergistically with the FtsZ-Targeting Agent TXA707 against Methicillin-Resistant Staphylococcus aureus. Antimicrob Agents Chemother. 2017 Aug 24;61(9). pii: AAC.00863-17. doi: 10.1128/AAC.00863-17. Print 2017 Sep. [PubMed:28630190]
  9. Sanbongi Y, Suzuki T, Osaki Y, Senju N, Ida T, Ubukata K: Molecular evolution of beta-lactam-resistant Haemophilus influenzae: 9-year surveillance of penicillin-binding protein 3 mutations in isolates from Japan. Antimicrob Agents Chemother. 2006 Jul;50(7):2487-92. [PubMed:16801430]
  10. Kumar P, Chauhan V, Silva JRA, Lameira J, d'Andrea FB, Li SG, Ginell SL, Freundlich JS, Alves CN, Bailey S, Cohen KA, Lamichhane G: Mycobacterium abscessus l,d-Transpeptidases Are Susceptible to Inactivation by Carbapenems and Cephalosporins but Not Penicillins. Antimicrob Agents Chemother. 2017 Sep 22;61(10). pii: AAC.00866-17. doi: 10.1128/AAC.00866-17. Print 2017 Oct. [PubMed:28760902]
  11. Moore BA, Jevons S, Brammer KW: Peptidoglycan transpeptidase inhibition in Pseudomonas aeruginosa and Escherichia coli by Penicillins and Cephalosporins. Antimicrob Agents Chemother. 1979 Apr;15(4):513-7. doi: 10.1128/aac.15.4.513. [PubMed:111613]
  12. Prober CG: Cephalosporins: an update. Pediatr Rev. 1998 Apr;19(4):118-27. doi: 10.1542/pir.19-4-118. [PubMed:9557062]
  13. Labro MT, el Benna J, Charlier N, Abdelghaffar H, Hakim J: Cefdinir (CI-983), a new oral amino-2-thiazolyl cephalosporin, inhibits human neutrophil myeloperoxidase in the extracellular medium but not the phagolysosome. J Immunol. 1994 Mar 1;152(5):2447-55. [PubMed:8133056]
  14. Cefdinir FDA label [Link]
  15. MSDS Cefdinir [Link]
  16. FDA Label: Apadaz [Link]
  17. Pfizer MSDS, Cefdinir [Link]
  18. Omnicef [Link]
  19. Appropriate prescribing of beta-lactamase antibiotics [Link]
  20. Dailymed: Cefdinir capsule [Link]
External Links
Human Metabolome Database
HMDB0014675
KEGG Drug
D00917
KEGG Compound
C08110
PubChem Compound
6915944
PubChem Substance
46505573
ChemSpider
5291705
ChEBI
3485
ChEMBL
CHEMBL927
Therapeutic Targets Database
DAP000436
PharmGKB
PA164768739
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
PDRhealth
PDRhealth Drug Page
Wikipedia
Cefdinir
ATC Codes
J01DD15 — Cefdinir
MSDS
Download (57 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
0CompletedTreatmentAcute, uncomplicated Appendicitis1
0RecruitingTreatmentOsteomyelitis1
1CompletedNot AvailableHealthy Volunteers4
1CompletedTreatmentHealthy Volunteers4
2, 3CompletedTreatmentAcute Otitis Media1
2, 3RecruitingTreatmentMastitis Acute Female1
4CompletedNot AvailableHealthy Volunteers3
4CompletedTreatmentAcute Bacterial Sinusitis (ABS)2
4CompletedTreatmentAcute Otitis Media2
4CompletedTreatmentMild to Moderate Uncomplicated Skin and Skin Structure Infections1
4RecruitingTreatmentAcute Exacerbation of Chronic Bronchitis (AECB) / Community-Acquired Pneumoniae1
4RecruitingTreatmentAntibiotics / Pituitary Adenomas1
4RecruitingTreatmentPneumonia1
Not AvailableCompletedTreatmentKwashiorkor / Marasmus1
Not AvailableCompletedTreatmentSnoring / Strep Throat1

Pharmacoeconomics

Manufacturers
  • Aurobindo pharma ltd
  • Lupin ltd
  • Orchid healthcare
  • Sandoz inc
  • Teva pharmaceuticals usa
  • Abbott laboratories
Packagers
  • Abbott Laboratories Ltd.
  • A-S Medication Solutions LLC
  • Aurobindo Pharma Ltd.
  • Ceph International Corp.
  • DAVA Pharmaceuticals
  • Dispensing Solutions
  • Diversified Healthcare Services Inc.
  • Greenstone LLC
  • Lupin Pharmaceuticals Inc.
  • Murfreesboro Pharmaceutical Nursing Supply
  • Northstar Rx LLC
  • Orchid Healthcare
  • PD-Rx Pharmaceuticals Inc.
  • Physicians Total Care Inc.
  • Redpharm Drug
  • Resource Optimization and Innovation LLC
  • Sandoz
  • Southwood Pharmaceuticals
  • Teva Pharmaceutical Industries Ltd.
Dosage forms
FormRouteStrength
CapsuleOral300 mg/1
Powder, for suspensionOral125 mg/5mL
Powder, for suspensionOral250 mg/5mL
Prices
Unit descriptionCostUnit
Omnicef 125 mg/5ml Suspension 100ml Bottle101.59USD bottle
Cefdinir 125 mg/5ml Suspension 60ml Bottle53.05USD bottle
Omnicef 300 mg capsule6.31USD capsule
Omnicef 300 mg omni-pac capsule5.72USD capsule
Cefdinir 300 mg capsule5.22USD capsule
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US4935507No1990-06-192011-12-04Us
Additional Data Available
  • Filed On
    Filed On

    The date on which a patent was filed with the relevant government.

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Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)>135https://www.trc-canada.com/product-detail/?CatNum=C242670
boiling point (°C)708.82https://cymitquimica.com/products/45-1097614/213978-34-8/cefdinir/
water solubility 8.85 ± 0.87 mg/mLhttps://www.mdpi.com/1420-3049/22/2/280/htm
logP-3.47https://aac.asm.org/content/47/2/689
pKa9.7https://www.chemicalbook.com/ChemicalProductProperty_US_CB7483101.aspx
Predicted Properties
PropertyValueSource
Water Solubility0.0878 mg/mLALOGPS
logP0.02ALOGPS
logP-1.7ChemAxon
logS-3.6ALOGPS
pKa (Strongest Acidic)1.74ChemAxon
pKa (Strongest Basic)7.45ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area158.21 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity94.34 m3·mol-1ChemAxon
Polarizability36.12 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption-0.7692
Blood Brain Barrier-0.9659
Caco-2 permeable-0.7205
P-glycoprotein substrateNon-substrate0.5185
P-glycoprotein inhibitor INon-inhibitor0.9298
P-glycoprotein inhibitor IINon-inhibitor0.9165
Renal organic cation transporterNon-inhibitor0.8919
CYP450 2C9 substrateNon-substrate0.8676
CYP450 2D6 substrateNon-substrate0.8203
CYP450 3A4 substrateNon-substrate0.5821
CYP450 1A2 substrateNon-inhibitor0.7603
CYP450 2C9 inhibitorNon-inhibitor0.8303
CYP450 2D6 inhibitorNon-inhibitor0.894
CYP450 2C19 inhibitorNon-inhibitor0.8044
CYP450 3A4 inhibitorNon-inhibitor0.8436
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.953
Ames testNon AMES toxic0.6686
CarcinogenicityNon-carcinogens0.8339
BiodegradationNot ready biodegradable0.9925
Rat acute toxicity1.8801 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9878
hERG inhibition (predictor II)Non-inhibitor0.8964
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
MS/MS Spectrum - , positiveLC-MS/MSsplash10-004i-2983000000-72bf1ac3398fbaa1531b

Taxonomy

Description
This compound belongs to the class of organic compounds known as cephalosporins. These are compounds containing a 1,2-thiazine fused to a 2-azetidinone to for a oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid moiety or a derivative thereof.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Lactams
Sub Class
Beta lactams
Direct Parent
Cephalosporins
Alternative Parents
N-acyl-alpha amino acids and derivatives / 2,4-disubstituted thiazoles / 1,3-thiazines / 2-amino-1,3-thiazoles / Tertiary carboxylic acid amides / Ketoximes / Heteroaromatic compounds / Secondary carboxylic acid amides / Amino acids / Azetidines
show 10 more
Substituents
Cephalosporin / N-acyl-alpha amino acid or derivatives / Alpha-amino acid or derivatives / 2,4-disubstituted 1,3-thiazole / Meta-thiazine / 1,3-thiazol-2-amine / Azole / Ketoxime / Tertiary carboxylic acid amide / Thiazole
show 24 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
cephalosporin, ketoxime (CHEBI:3485)

Targets

Kind
Protein
Organism
Neisseria gonorrhoeae
Pharmacological action
Yes
Actions
Inhibitor
General Function
Penicillin binding
Specific Function
Synthesis of cross-linked peptidoglycan from the lipid intermediates.
Gene Name
penA
Uniprot ID
P08149
Uniprot Name
Penicillin-binding protein 2
Molecular Weight
63649.54 Da
References
  1. Ochiai S, Sekiguchi S, Hayashi A, Shimadzu M, Ishiko H, Matsushima-Nishiwaki R, Kozawa O, Yasuda M, Deguchi T: Decreased affinity of mosaic-structure recombinant penicillin-binding protein 2 for oral cephalosporins in Neisseria gonorrhoeae. J Antimicrob Chemother. 2007 Jul;60(1):54-60. Epub 2007 May 31. [PubMed:17540669]
  2. Ferrer-Gonzalez E, Kaul M, Parhi AK, LaVoie EJ, Pilch DS: beta-Lactam Antibiotics with a High Affinity for PBP2 Act Synergistically with the FtsZ-Targeting Agent TXA707 against Methicillin-Resistant Staphylococcus aureus. Antimicrob Agents Chemother. 2017 Aug 24;61(9). pii: AAC.00863-17. doi: 10.1128/AAC.00863-17. Print 2017 Sep. [PubMed:28630190]
Kind
Protein
Organism
Haemophilus influenzae
Pharmacological action
Yes
Actions
Inhibitor
General Function
Penicillin binding
Specific Function
Not Available
Gene Name
pbp3
Uniprot ID
Q60FT7
Uniprot Name
PBP3
Molecular Weight
67295.025 Da
References
  1. Sanbongi Y, Suzuki T, Osaki Y, Senju N, Ida T, Ubukata K: Molecular evolution of beta-lactam-resistant Haemophilus influenzae: 9-year surveillance of penicillin-binding protein 3 mutations in isolates from Japan. Antimicrob Agents Chemother. 2006 Jul;50(7):2487-92. [PubMed:16801430]
  2. Ferrer-Gonzalez E, Kaul M, Parhi AK, LaVoie EJ, Pilch DS: beta-Lactam Antibiotics with a High Affinity for PBP2 Act Synergistically with the FtsZ-Targeting Agent TXA707 against Methicillin-Resistant Staphylococcus aureus. Antimicrob Agents Chemother. 2017 Aug 24;61(9). pii: AAC.00863-17. doi: 10.1128/AAC.00863-17. Print 2017 Sep. [PubMed:28630190]
  3. Tristram S, Jacobs MR, Appelbaum PC: Antimicrobial resistance in Haemophilus influenzae. Clin Microbiol Rev. 2007 Apr;20(2):368-89. doi: 10.1128/CMR.00040-06. [PubMed:17428889]
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Inhibitor
General Function
Peroxidase activity
Specific Function
Part of the host defense system of polymorphonuclear leukocytes. It is responsible for microbicidal activity against a wide range of organisms. In the stimulated PMN, MPO catalyzes the production o...
Gene Name
MPO
Uniprot ID
P05164
Uniprot Name
Myeloperoxidase
Molecular Weight
83867.71 Da
References
  1. Labro MT, el Benna J, Charlier N, Abdelghaffar H, Hakim J: Cefdinir (CI-983), a new oral amino-2-thiazolyl cephalosporin, inhibits human neutrophil myeloperoxidase in the extracellular medium but not the phagolysosome. J Immunol. 1994 Mar 1;152(5):2447-55. [PubMed:8133056]
4. Peptidoglycan transpeptidase
Kind
Group
Organism
Not Available
Pharmacological action
Unknown
Actions
Inhibitor
The enzyme peptidoglycan transpeptidase, which catalyzes cell wall cross-linking of bacteria.
References
  1. Kumar P, Chauhan V, Silva JRA, Lameira J, d'Andrea FB, Li SG, Ginell SL, Freundlich JS, Alves CN, Bailey S, Cohen KA, Lamichhane G: Mycobacterium abscessus l,d-Transpeptidases Are Susceptible to Inactivation by Carbapenems and Cephalosporins but Not Penicillins. Antimicrob Agents Chemother. 2017 Sep 22;61(10). pii: AAC.00866-17. doi: 10.1128/AAC.00866-17. Print 2017 Oct. [PubMed:28760902]
  2. Moore BA, Jevons S, Brammer KW: Peptidoglycan transpeptidase inhibition in Pseudomonas aeruginosa and Escherichia coli by Penicillins and Cephalosporins. Antimicrob Agents Chemother. 1979 Apr;15(4):513-7. doi: 10.1128/aac.15.4.513. [PubMed:111613]

Transporters

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Symporter activity
Specific Function
Sodium-ion dependent, high affinity carnitine transporter. Involved in the active cellular uptake of carnitine. Transports one sodium ion with one molecule of carnitine. Also transports organic cat...
Gene Name
SLC22A5
Uniprot ID
O76082
Uniprot Name
Solute carrier family 22 member 5
Molecular Weight
62751.08 Da
References
  1. Ganapathy ME, Huang W, Rajan DP, Carter AL, Sugawara M, Iseki K, Leibach FH, Ganapathy V: beta-lactam antibiotics as substrates for OCTN2, an organic cation/carnitine transporter. J Biol Chem. 2000 Jan 21;275(3):1699-707. [PubMed:10636865]
  2. Tein I: Carnitine transport: pathophysiology and metabolism of known molecular defects. J Inherit Metab Dis. 2003;26(2-3):147-69. [PubMed:12889657]
  3. HMDB database, Cefdinir [Link]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
General Function
Proton-dependent oligopeptide secondary active transmembrane transporter activity
Specific Function
Proton-coupled intake of oligopeptides of 2 to 4 amino acids with a preference for dipeptides. May constitute a major route for the absorption of protein digestion end-products.
Gene Name
SLC15A1
Uniprot ID
P46059
Uniprot Name
Solute carrier family 15 member 1
Molecular Weight
78805.265 Da
References
  1. Ganapathy ME, Prasad PD, Mackenzie B, Ganapathy V, Leibach FH: Interaction of anionic cephalosporins with the intestinal and renal peptide transporters PEPT 1 and PEPT 2. Biochim Biophys Acta. 1997 Mar 13;1324(2):296-308. [PubMed:9092716]
  2. Terada T, Saito H, Mukai M, Inui K: Recognition of beta-lactam antibiotics by rat peptide transporters, PEPT1 and PEPT2, in LLC-PK1 cells. Am J Physiol. 1997 Nov;273(5 Pt 2):F706-11. [PubMed:9374833]
  3. Tsuji A: Transporter-mediated Drug Interactions. Drug Metab Pharmacokinet. 2002;17(4):253-74. [PubMed:15618677]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Peptide:proton symporter activity
Specific Function
Proton-coupled intake of oligopeptides of 2 to 4 amino acids with a preference for dipeptides.
Gene Name
SLC15A2
Uniprot ID
Q16348
Uniprot Name
Solute carrier family 15 member 2
Molecular Weight
81782.77 Da
References
  1. Ganapathy ME, Prasad PD, Mackenzie B, Ganapathy V, Leibach FH: Interaction of anionic cephalosporins with the intestinal and renal peptide transporters PEPT 1 and PEPT 2. Biochim Biophys Acta. 1997 Mar 13;1324(2):296-308. [PubMed:9092716]
  2. Terada T, Saito H, Mukai M, Inui K: Recognition of beta-lactam antibiotics by rat peptide transporters, PEPT1 and PEPT2, in LLC-PK1 cells. Am J Physiol. 1997 Nov;273(5 Pt 2):F706-11. [PubMed:9374833]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
Curator comments
Data in the literature regarding this transporter action for this drug are limited.
General Function
Sodium-independent organic anion transmembrane transporter activity
Specific Function
Involved in the renal elimination of endogenous and exogenous organic anions. Functions as organic anion exchanger when the uptake of one molecule of organic anion is coupled with an efflux of one ...
Gene Name
SLC22A6
Uniprot ID
Q4U2R8
Uniprot Name
Solute carrier family 22 member 6
Molecular Weight
61815.78 Da
References
  1. Kim YC, Kim IB, Noh CK, Quach HP, Yoon IS, Chow ECY, Kim M, Jin HE, Cho KH, Chung SJ, Pang KS, Maeng HJ: Effects of 1alpha,25-dihydroxyvitamin D3 , the natural vitamin D receptor ligand, on the pharmacokinetics of cefdinir and cefadroxil, organic anion transporter substrates, in rat. J Pharm Sci. 2014 Nov;103(11):3793-3805. doi: 10.1002/jps.24195. Epub 2014 Sep 29. [PubMed:25266751]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
Curator comments
Data in the literature regarding this transporter action for this drug are limited.
General Function
Sodium-independent organic anion transmembrane transporter activity
Specific Function
Plays an important role in the excretion/detoxification of endogenous and exogenous organic anions, especially from the brain and kidney. Involved in the transport basolateral of steviol, fexofenad...
Gene Name
SLC22A8
Uniprot ID
Q8TCC7
Uniprot Name
Solute carrier family 22 member 8
Molecular Weight
59855.585 Da
References
  1. Wang H, Sun P, Wang C, Meng Q, Liu Z, Huo X, Sun H, Ma X, Peng J, Liu K: Pharmacokinetic changes of cefdinir and cefditoren and its molecular mechanisms in acute kidney injury in rats. J Pharm Pharmacol. 2018 Nov;70(11):1503-1512. doi: 10.1111/jphp.12994. Epub 2018 Jul 25. [PubMed:30047127]
  2. Kim YC, Kim IB, Noh CK, Quach HP, Yoon IS, Chow ECY, Kim M, Jin HE, Cho KH, Chung SJ, Pang KS, Maeng HJ: Effects of 1alpha,25-dihydroxyvitamin D3 , the natural vitamin D receptor ligand, on the pharmacokinetics of cefdinir and cefadroxil, organic anion transporter substrates, in rat. J Pharm Sci. 2014 Nov;103(11):3793-3805. doi: 10.1002/jps.24195. Epub 2014 Sep 29. [PubMed:25266751]
  3. Ueo H, Motohashi H, Katsura T, Inui K: Human organic anion transporter hOAT3 is a potent transporter of cephalosporin antibiotics, in comparison with hOAT1. Biochem Pharmacol. 2005 Oct 1;70(7):1104-13. doi: 10.1016/j.bcp.2005.06.024. [PubMed:16098483]

Drug created on June 13, 2005 07:24 / Updated on November 02, 2019 04:30